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Yes, You Can Take a Vacation. Here’s How.

I’m on vacation! A real one!

Not just a little day trip to Spain like a couple weeks ago. But a plane (a couple, actually)! And sunshine! And beaches! And no schedule!

Freelancing freedom, is really what I’m trying to create for myself and help you create too. (It’s not just a name that sounded good so I bought the url and went with it)

And freedom for me, means taking vacation. When I want and where I want. (Asking for time off at my corporate job always felt like a selfish unacceptable thing to do- no matter how much I deserved it or was legally entitled to it.)

So you may be thinking, well if you’re really taking a vacation, why are you spending time writing this blog post?

Well ya see, I’m not 🙂

I’ll let you in on a little secret:

This post is scheduled.

I wrote it a few days ago. Thanks to the technology gods that make this freelance freedom possible, you get to read it now (while I’m on the beach drinking a mojito). Which means my business can still run and I get to enjoy some freedom away from it.

The truth is, this first real year in business, I haven’t really taken a proper vacation. I’m willing to bet you haven’t either. It takes awhile to go from crazy-I-have-to-make-this-work-hustle to I’ve-made-it-time-to-enjoy-the-fruits-of-my-labor.

And honestly, I’m not quite there yet. I’m still in the work-aholic stage of being a freelancer. But I’m getting closer, albeit slowly.

As I head off to taste a little freelancing freedom, I thought I’d share with you a few tips on preparing to take a vacation as an online freelancer so you can see that it is, in fact possible.

Hopefully this can help you take more vacation too.

Let Your Clients Know as Early as Possible

Whether it’s a last minute trip or planned in advance, let your clients know as soon as you know and be sure to remind them when you get closer to the date.

I’ve seen some seasoned freelancers even have on their work with me page the available months for booking and the months they’ll be on vacation. Hopefully next year I’ll be organized enough to say “I don’t work May, August & September” so it’s clear up front!

Of course the dream is to finish up all in-progress projects before you leave, but that’s not always the reality. Just be open and honest and they’ll understand!

Pre-Write and Schedule Your Blog Posts & Newsletter

WPScheduleInstead of letting your traffic slide while you’re away, pre-write your blog posts and newsletters and schedule them to post while you’re on the beach. Just like this one!

You can use the native WordPress scheduler alongside a plugin like WP Editorial Calendar  to schedule and stay organized.

And if batch writing posts in advance is a little daunting for you, enlist a guest poster or two to take the stage while you’re away.

I’ve got a couple lovely FTF members who I’ve brought on to share their wisdom with you guys while I’m away. I get a break, they get to share with a new audience, and you get a break from me 🙂 Win win all around!

Schedule Social Media Updates

If you’ve spent time building up your reach, engagement and social media audience, it’d be a shame to lose that momentum during your vacation. Although not all platforms function the same way, Facebook in particular can give you some trouble if you suddenly disappear.

Use Buffer or Hootsuite to pre-schedule some helpful content for your fans, so your reach doesn’t drop off the face of the earth while you’re away. You’ll likely check in (unless you’re one of those amazing people who can go completely offline while away), engage and add updates about your trip, but this way you are still providing regular useful content to your followers.

Need tips on scheduling? Jackie Johnstone’s blog posts  and webinar made my social media life so much easier.

Accept that you might have a lower month in terms of income.

That’s the life of a freelancer, vacation or not. Especially if you have longer term contracts that aren’t invoiced 100% up front.

Outright-graphLooking at my year graph in Outright, I could easily have a heart attack, seeing how low this month will be.

But the reality is, I invoiced some clients on the 31st of last month that could have easily been invoiced on June 1st. And I’ve finished up some projects that I could have invoiced if I wasn’t on vacation right now, and instead I’ll invoice them in July.

If tracking money is important to you (and it should be) it’s the yearly amount that should matter. Not any given month. Some months are amazing and some months not so much (even if you’re actively working non-stop). Luckily I’m not a crazy spender- so a good month doesn’t mean a shopping spree and I know I need to keep enough aside if ever the next month is a bit dry.


You may think your business is going to tank if you step away for even a day, let alone a couple weeks. Wrapping things up before leaving and preparing for time away can be extra work. But hey, it’s worth it! That’s why you’re building this business for in the first place right?

Freedom. So prepare and then enjoy it.

So tell me

Do you take enough vacation as a freelancer? How do you prepare to take a break from your biz?


P.S. Follow me on Instagram to see what I’m up to while I’m away from biz!

Leah Kalamakis Leah Kalamakis is the founder of The Freelance To Freedom Project and a web designer/developer for brilliant entrepreneurs. When she’s not hanging out in the FTF Community, you can find her people watching on the streets of NYC. Come say hi on Twitter, Instagram, or Facebook.

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{ 10 comments… add one }
  • Scheduling content is so important! Even when I’m not on vacation, it helps free up my plate for other things so I’m not like “did I schedule that blog? Did I share that post?” I’ll be at my sister-in-law’s wedding this weekend and I want to be able to disconnect, so I’ve already scheduled some content to go out the next few days. Not quite a vacation, but still something I want to disconnect for.

  • Yay!! Enjoy your vacation!

    I just took my first vacation as a freelancer two weeks ago, and loved it. In my corporate job, there was a not-quite-unspoken understanding that anyone on vacation was still expected to check email regularly, answer calls, and get to the laptop if something needed review, especially in the summer busy season. Needless to say, this was not conducive to quality family time.

    This year, I let my clients know ahead of time, I reminded them regularly and, when I went away, everyone wished me well and insisted that I really try to relax. It was amazing!

    At the end, my husband and I reflected on how I had disconnected completely and experienced no stress or anxiety around leaving my work. I definitely have had some self-talk around being ok with a lower income this month, but it is totally worth it. Here’s to freelancing freedom for all of us!

  • ACK! I love the little “eek” image with income.

    Don’t worry – with vacation in your blood you’ll be stronger than ever.

  • I’m trying to take a vacation this year! Haven’t really had one since I started my biz–unless you count working vacations. I was even having to check emails during my wedding! Oi! So this year my goal is to take at least a full week OFF with no emails or anything!

  • This is so timely! I just went on my first vacation since starting my business. Overall, I was able to plan it so I didn’t have much work to do, but it did push me closer to my goal to hire an assistant. It would have been a lot easier to relax if I knew that someone had an eye on things while I was vacationing. =)

  • Dave Waterman

    Thanks, I don’t usually comment much but there’s some useful scheduling stuff here
    many thanks

  • Absolutely! It has to be part of your freelance business process (can you tell I love systems lol). I include it in my welcome letter to clients when they first onboard giving them a heads up and I send out an email 30 days in advance (actually considering pushing this out to 60) with a follow-up 2 weeks before I leave and a final hey remember I won’t be here next week. I also schedule those to go out through my email marketing platform to my clients because you get the occasional oh you didn’t tell me that what I am supposed to do client and I go yeah you opened it on xxxx lol

    Anyhoo, enjoy! I’m looking forwarding to my time off next month!

    PS – One thing to add to this amazing list is make sure your electronic appointment scheduler is updated so the times you are away no one can book an appointment. Nothing worse than a potential new client booking a discovery call during a period you won’t be around.

    • Leah Kalamakis Leah Kalamakis

      Ahh yes – the scheduler mishap is unfortunate! Great tip to add!

  • So helpful – thank you for the scheduling resources!

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